ethyl 2-nitro-5-oxohexanoate | 79195-01-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-nitro-5-oxohexanoate
• CAS: 79195-01-0
• 化学式: C₈H₁₃NO₅
• 分子量: 203.195
• InChiKey: BJJADLSVJVQNIA-UHFFFAOYSA-N

物化性质

• 沸点：
  317.2±27.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-nitro-5-oxohexanoate 在 potassium fluoride 、 sodium hydroxide 、 过氯酰氟 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 辛腈,4-氟-4-硝基-7-羰基-
  参考文献：
  名称：

  Chemistry of novel compounds with a multifunctional carbon structure. 5. Molecular design of versatile building blocks for aliphatic monofluoro molecules by manipulation of multifunctional carbon structure

  摘要：

  DOI：

  10.1021/jo00284a017
• 作为产物：
  描述：

  硝基乙酸乙酯 以54%的产率得到
  参考文献：
  名称：

  TAKEUCHI, YOSHIO;NAGATA, KAZUHIRO;KOIZUMI, TORU, J. ORG. CHEM., 54,(1989) N3, C. 5453-5459

  摘要：

  DOI：

文献信息

• Rapid synthesis of substituted pyrrolines and pyrrolidines by nucleophilic ring closure at activated oximes
  作者：Nandkishor Chandan、Amber L. Thompson、Mark G. Moloney

  DOI：10.1039/c2ob26423d

  日期：——

  Substituted pyrrolines are available by ring closure initiated by direct nucleophilic attack of stabilized enolates at the nitrogen of oximes activated with a leaving group, in a process which effectively out-competes the more usual Beckmann rearrangement. Subsequent reduction provides diastereoselective access to the corresponding pyrrolidines. This provides a rapid route to saturated heterocyclic

  取代的吡咯啉可通过闭环反应来获得，该闭环反应是由稳定的烯醇酸酯在离去基团激活的肟的氮原子上进行亲核攻击而发起的，该过程可有效地胜过更常见的贝克曼重排。随后的还原提供非对映选择性地进入相应的吡咯烷。这提供了从容易获得的前体到饱和杂环系统的快速途径。
• Michael Additions versus Cycloaddition Condensations with Ethyl Nitroacetate and Electron-Deficient Olefins
  作者：Elena Trogu、Francesco De Sarlo、Fabrizio Machetti

  DOI：10.1002/chem.200802652

  日期：2009.8.10

  nitroacetate (1) reacts with electron‐poor olefins in the presence of a base to give either the Michael adducts 3 or the isoxazoline cycloadducts 4, resulting from water elimination. The proportions of the two products depend on the reaction conditions and change in the course of the process. Kinetic profiles for the two reactions show that the cycloaddition‐condensations require long induction times that dramatically

  硝基乙酸乙酯 ( 1 ) 与缺电子烯烃在碱存在下反应生成迈克尔加合物3或异恶唑啉环加合物4，这是由水消除产生的。两种产物的比例取决于反应条件和过程过程中的变化。两种反应的动力学曲线表明，环加成-缩合需要较长的诱导时间，在向催化体系中加入铜盐后会显着减少：诱导时间的下降导致环加合物4的比例增加，这通常是唯一的反应产物。这是关于选择性形成产品3和4的第一份报告通过调节催化系统从初级硝基化合物中提取。
• Hydrogen-Bond-Promoted C-C Bond-Forming Reaction: Catalyst-Free Michael Addition Reactions in Ethanol
  作者：Seiji Shirakawa、Shoichi Shimizu

  DOI：10.1055/s-2007-992377

  日期：——

  A practical protocol for catalyst-free Michael addition reactions in ethanol was developed. The reaction was promoted efficiently in alcohol without any additives, and the importance of hydrogen-bonding activation was suggested.

  开发了一种在乙醇中无需催化剂的迈克尔加成反应实用方案。该反应在无任何添加剂的醇中高效进行，并提示了氢键活化的重要性。
• Conjugate Addition versus Cycloaddition/Condensation of Nitro Compounds in Water: Selectivity, Acid-Base Catalysis, and Induction Period
  作者：Luca Guideri、Francesco De Sarlo、Fabrizio Machetti

  DOI：10.1002/chem.201202698

  日期：2013.1.7

  react in water as in chloroform with electron‐deficient dipolarophiles to give condensation or conjugate addition products under base catalysis. In general, high selectivity towards condensation is observed in water, with shorter induction periods than in chloroform. In water, condensations slowly occur even without base; kinetic profiles evidence the catalytic effect of the base, which should be related

  硝基乙酸盐和硝基乙酰胺在水中（如氯仿中）与缺电子的双极性亲和剂反应，在碱催化下生成缩合或共轭加成产物。通常，在水中观察到对缩合的高选择性，诱导时间比在氯仿中短。在水中，即使没有碱，凝结也会缓慢发生。动力学曲线证明了碱的催化作用，这与转化为互变异构体硝酸有关。水中的冷凝可方便地获得带有各种官能团（包括铵，羧基和羧酰胺）的异恶唑衍生物。
• Poly(N-vinylimidazole) as efficient recyclable catalyst for the Michael addition of CH-acids to electron deficient alkenes in water
  作者：E. A. Tarasenko、V. S. Tyurin、F. Lamaty、I. P. Beletskaya

  DOI：10.1007/s11172-011-0401-7

  日期：2011.12

  Efficiency of poly(N-vinylimidazole) as the basic recyclable catalyst for the Michael addition of CH-acids to acrylonitrile, methyl acrylate, methyl vinyl ketone and methyl vinyl sulfone in water at ambient temperature was studied. In these reactions, formation of both 1: 1 and 1: 2 adducts is possible.

  研究了聚（N-乙烯基咪唑）作为碱性可回收催化剂的效率，用于在环境温度下将 CH 酸与丙烯腈、丙烯酸甲酯、甲基乙烯基酮和甲基乙烯基砜在水中进行迈克尔加成。在这些反应中，可能形成 1:1 和 1:2 加合物。